The Landlording Show - Episode 18 - From House Hacking to Private Lending: With Bryce Matheson In this episode, host Tim Harstead sits down with Bryce Matheson from Holbrook Capital to discuss Bryce’s journey from house hacking to managing millions in real estate investments. They dive into essential strategies for new and experienced investors, highlighting the value of long-term planning, creative financing, and transitioning to lending for passive income. Key Takeaways: The Evolution from House Hacking to High-Capital Lending: Bryce shares his journey, starting with his first rental property and eventually scaling to a multi-million-dollar portfolio. Building a Sustainable Portfolio: Tips on financing multiple properties, handling property flips, and knowing when to expand or pivot. The Pros and Cons of Self-Management vs. Property Management: Why Bryce self-managed dozens of units and what he learned along the way. Passive Income through Lending: Discover why Bryce ultimately transitioned to real estate lending and how it allowed him to continue growing his wealth with less hassle. Whether you’re investing in Chicago or elsewhere, this episode is packed with actionable insights for anyone looking to grow their real estate portfolio or diversify through lending.